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Description
TCI D4736 with CAS number 5398-27-6 is 2,6-Diiodo-4-nitroaniline, a non-heterocyclic aromatic building block carrying a primary amine group, two iodine atoms at the ortho positions, and a nitro group at the para position. The compound serves as a valuable starting material for organic synthesis laboratories because it presents three distinct reaction sites on a single benzene ring. The combination of a strongly electron-withdrawing group with heavy halides makes it an attractive choice for constructing complex molecules, ranging from pharmaceutical intermediates through to materials with specific optical and electronic properties.
The most notable characteristic of this building block is the reactivity of its two iodine atoms. Carbon–iodine bonds are relatively weak compared with carbon–bromine or carbon–chlorine bonds, so oxidative activation by palladium or copper catalysts proceeds more readily and cross-coupling reactions can often be run at lower temperatures. This is advantageous when working with heat-sensitive substrates. Meanwhile, the nitro group at the para position provides strong electron withdrawal while also acting as an amine precursor through reduction, and the primary amine group can be acylated, sulfonylated, or diazotised according to the synthetic design.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, medicinal chemistry, and functional materials, as well as in industrial R&D units developing new intermediates. It suits work in which a single reagent must deliver several orthogonal handles, allowing researchers to build target scaffolds in fewer steps. Because the compound is supplied by TCI, it fits laboratories that rely on consistent, well-documented reagents for reproducible multi-step synthetic routes.
Laboratory Applications
Palladium-catalysed cross-coupling — the two ortho iodine atoms undergo oxidative addition readily, enabling Suzuki, Sonogashira, or Heck couplings to be run under milder thermal conditions than bromo or chloro analogues would require.
Synthesis of pharmaceutical intermediates — three distinct reactive positions on one benzene ring let medicinal chemistry groups assemble substituted aniline scaffolds efficiently, shortening multi-step routes toward candidate molecules and their analogue series.
Preparation of functional optical and electronic materials — the strongly electron-withdrawing nitro group combined with heavy iodine substituents supports the construction of conjugated and push–pull systems with targeted optical and electronic behaviour.
Nitro group reduction chemistry — the para nitro function acts as a masked amine, allowing laboratories to introduce a second amino group at a chosen stage of the sequence and diversify the resulting diamine products.
Amine derivatisation and diazotisation work — the primary aromatic amine can be acylated, sulfonylated, or converted to a diazonium species, giving synthesis groups a flexible entry point for amides, sulfonamides, and further substitution products.
Specifications
Brand: TCI
CAS number: 5398-27-6
Chemical name: 2,6-Diiodo-4-nitroaniline
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes: available in standard TCI catalogue research pack sizes; please confirm the required packaging when ordering
Storage: keep in the original tightly closed container, protected from light, in a cool, dry, well-ventilated chemical store
Handling and Storage
Store the material in its original tightly closed container in a cool, dry, well-ventilated area away from direct sunlight and heat sources, since iodinated aromatic nitro compounds are best protected from light and elevated temperatures. Amber glass or the supplier's original packaging is suitable; avoid transferring the solid into containers that are not chemically compatible. Handle the compound inside a fume hood using nitrile gloves, safety glasses, and a laboratory coat, and avoid generating dust when weighing. Keep it separated from strong reducing agents and strong bases, label all secondary containers clearly, and consult the manufacturer's safety data sheet before use and before disposing of residues through the laboratory's chemical waste stream.
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